Mastering Monopoly: Advanced Strategies to Win Every Time

In this advanced version of the „How to Win Monopoly Every Time“ video, the journalist explains the strategic approach to buying properties, timing trades, controlling the money supply, and using various strategies to win the game with any property set. The video analyzes the cost and potential rent of different property sets, emphasizing the importance of speed of development. It also highlights the significance of the number of players and the money supply in determining trade timing. The journalist concludes by emphasizing the versatility of these strategies, enabling players to win with any property set.

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Key Insights:

  • The speed of property development is crucial in Monopoly.
  • Orange and red property sets are the most desirable due to their balance of cost and rent potential.
  • Boardwalk, despite being the most expensive property, can be one of the cheapest to develop.
  • The timing of trades is important, especially in anticipating the future development of property sets.
  • The money supply in the game should be considered when making trades.
  • Pigeonholing houses can put opponents in difficult situations where they may have to sell houses.
  • The utilities are generally considered to be weak properties.
  • The railroads can be useful for generating income and disrupting opponents‘ cash flow.
  • Each property set has its own strengths and weaknesses, and strategies should be tailored accordingly.
  • Striking quick with a fast monopoly or defending for a slow monopoly are both viable winning strategies.
  • Understanding dice probability and making strategic moves based on opponents‘ positions is key.
  • Controlling the money supply can give you a significant advantage in the game.
  • The video aims to provide comprehensive insights to make players unstoppable in Monopoly.


This video is the advanced version of how to win Monopoly every time. We’ll assume you’ve already watched the first video and immediately move forward. If you haven’t, the link to the video is in the description.

First, this video is going to show you why to buy certain properties and not others. Then, we’ll go over the timing of trades to get yourself better deals. After that, we’ll discuss how to control the money supply and pigeonhole houses on your opponent. Finally, we’ll learn how to pull each and every strategy together to win the game with any property set.

There are over 10,000 moving parts in this video, each done by hand, as well as decades worth of Monopoly knowledge made to make it the best Monopoly video possible. If you gain value from this video, give it a like. It helps the YouTube algorithm. Also, write a comment about anything. YouTube likes that too. And if you want to help the channel grow, hit subscribe. If this video brings in over 5,000 new subscribers, I’ll make a new „How to Win“ video on whichever game is asked for the most in the comments.

Now, let’s look at why we should buy some properties and not others. We’ll start by comparing the two best property sets, orange and red. Orange is roughly one roll past jail, the most likely spot on the board to land. Red is roughly two rolls past jail. While rate of return is a good metric we want to take into consideration, we also need to consider the impact on the game. If we can make quick money, it not only helps us, but it also makes it more difficult for other players to buy or develop properties. So, the speed at which we can develop our properties needs to be taken into consideration as well.

Assuming we pay sticker price for each property set, the oranges will cost $560 for all properties, $1,460 for all with three houses (which is our sweet spot), and $2,060 for hotels. Bear in mind, we start the game with $1,500. For the Reds, it will cost $680 for all properties, $2,030 for three houses, and $2,930 for hotels. Given that you start the game with $1,500, you should start to see where much of the problem lies and why speed of development is important. Hotels are a luxury and shouldn’t be built until you have a firm grip on the lead. So, we’ll analyze the properties from the perspective of three houses.

However, just for fun, for the same money, you can put hotels on Orange and get a thousand rent, or three houses on Red and get just 750 in rent. The Reds, in this case, are actually more dangerous because they can still carry more houses and thus have higher rent. But the main distinction here is the speed of development. If you start with $1,500, where is the rest of your money going to come from? Most of it early on will just come from passing go, which will take several turns. With just our initial money, we can top out at a return of $600 on New York Avenue, or a return of just $300 on Illinois Avenue. The rent of $600 provides cash for six more houses on orange, while the $300 provides only enough for two more houses on red. This dynamic is the beginning of pigeonholing houses, essentially binding your opponent into a catch-22 situation.

If they don’t buy houses, the properties can’t do anything. But if they do buy houses, they’re put in situations where they might have to sell them, which is a major no-no. This speed of development is important. So, if we look at properties that have great speed, oranges can top at a $600 rent. With your initial money, you can actually crack a fourth house on one of the pinks with a $700 rent. Because of property prices, though, the positioning of orange is better.

The light blues can top out with hotels for just $1,070, with a hotel rent of $600. Their positioning before jail is a disadvantage, but with how quickly this can be developed, it can be a major advantage early in the game. Baltic can hit $450 with a hotel. It’s cheap but doesn’t pack much of a punch. Its position on the board makes it difficult to land on. It’s generally better to use your money developing other properties than buying houses on Baltic.

Now, let’s talk about a property you probably weren’t thinking about: Boardwalk. Yes, the most expensive property on the board is actually one of the cheapest to develop. With your initial cash, you can get a rent of $600 on Boardwalk. This is because blue only has two properties to develop. The disadvantage to blue is that the odds are not particularly high to roll there. But if you do get a $600 rent, you can afford three or more houses, and the rent suddenly becomes $1,400, which is going to give anyone a bad day if they land on it. Owning blue in this capacity is risky, but it’s also why you shouldn’t overlook these properties or simply let someone else own them without defending yourself.

The speed of development plays a major factor in what you should buy and not buy. The yellows and especially the greens are very slow to develop. But rest assured, you do not want to land on these property sets if they have several houses. Given these dynamics, brown is generally not worth it. Your money is more useful in buying houses elsewhere. Light blue is great if you get it very early, like less than passing go three times. Pink is likely the worst monopoly on the buy side. Its value comes if you can develop houses here while no one else can develop houses elsewhere. Since it’s only three or four spots past jail, players usually roll right past it if they’re getting out of jail. But you do have to keep tabs on the Saint Charles Place card so that you don’t get surprised.

Orange is the best, given the balance of cost to develop and rent prices, and also sits on the hottest area of the board. Red is also in a hot area of the board and has the Illinois Avenue chance card. But as explained, the cost to develop is high, so if someone else gets houses first, you might find yourself stuck with one or two houses without the money needed to get to three. Yellow is just as expensive but in a colder part of the board, meaning it’ll take many laps around the board to develop these. Green is a colder, more expensive yellow. The only way to utilize green is in a very slow game where no one wants to trade and many laps around the board happen. The rent is so high here that if there aren’t other houses to threaten you, you can inch house by house, collecting go money and rent, until you reach three or more houses. This is very slow, but if you reach this point, these can become very scary. However, these properties are typically not worth the money unless the game is very slow.

On the other hand, blue utilizes two properties in the set to create massive rents. The „Take a Walk on the Boardwalk“ card will take the wind out of anyone’s sails. On their own, though, they can be frustrating because they’re hard to land on, especially Park Place. You can find yourself feeling very unlucky that no one is landing on your properties and that all you need is one more rent to win. Watch out for that. That’s why it’s good to pair these with something like the railroads. The more players in a game, the more valuable the railroads become. This is twofold: there are more people to land on them, and there’s more competition for the other monopolies, leading to a slower game where players have more cash. The railroads don’t make you rich; they just keep other players‘ money in check and siphon money to you to purchase houses with. They also make it more dangerous for others to buy houses since if you have four railroads, every single player’s turn stands the risk of landing on a railroad and paying you $200. This makes railroads useful to have but shouldn’t be your main focus.

Lastly, the utilities are just plain awful. They aren’t even good for trades. In the last video, we discussed trades, but now we’re going to look at the timing of trades. Your first few properties are random and based purely on luck. Your next few properties are based on skill and should consider ease of trade. Trading for the first orange won’t be that hard because it’s not very powerful. The second orange will be harder but not the end of the world. Then, the third orange will fight you tooth and nail and want the farm. It’ll make sense to anticipate which properties you might later want. If you hold one orange, you might want to trade now in the hopes of landing on the third one because you might not get it later. Or, if you have another player with good odds of landing on their second orange and you’re playing with AI, you might want to make a defensive trade now because the AI in Monopoly is not smart at all.

It’s also important to keep an eye on the money supply. The number of players you have will affect this. If you have three players, there’s $4,500 in starting cash. If there are six players, there’s $9,000 in starting cash. The timing of your trades can play a big factor in the money supply. For example, let’s play out the defensive trade from the first video. Your opponent isn’t happy you stopped him from completing his Monopoly, but now the game has changed. Everyone is poor, including you. You ended up with the yellows with one house already but don’t have much money to do much.

Here’s a scenario where you can use the money supply to hijack the game out of the kindness of your heart. You trade St. James Place for $300 and B&O Railroad. This allows you cash to reach two houses, and the opponent doesn’t have much ability to develop the oranges. You are actually dumping a good property on your opponent on purpose. First, it allows you to get the money to make your Monopoly dangerous, even if it’s not the best one. Second, you’re going to pigeonhole houses. You still need at least $150 more for another house, and your Monopoly isn’t in a hot area of the board. However, your opponent can’t build houses past „Go“ as it will only give them $200 in rent with one house, which is only $80. Let’s say the opponent is lucky and passes your properties three separate times in a row and collects „Go“ three times. Putting it all on houses gets them a rent of $220. Your rent is still $330. Luck can only last so long.

So, on the fourth pass, the opponent finally lands on your yellow properties. The opponent needs to get that money from somewhere to acquire $300. They would have to sell all six houses, setting them back to the start. You can set other players in this loop by withholding properties they want and then dumping them on them when the time is right. If the opponent doesn’t buy those houses, then you have nothing to worry about. And if they do buy them, then they’re taking a large risk.

This example is for the yellows, and the trade in the previous video is with pinks for a reason. You can win with every property set. All you have to do is either strike quickly with a fast Monopoly or defend the game long enough to win with a slow Monopoly. If you’re striking with a quick Monopoly, you want to get it up quickly so you can start collecting high rents to control the money supply. And if you’re working with a slow Monopoly, make defensive trades to eliminate competition. Remember your odds of dice probability and make moves like buying houses when your opponents are close, or if you’re going to dump a property like orange on your opponent, maybe you pass that color set first before you do it.

You won’t want to do a property dump if you have a low-hitting property set like brown or a set with a low likelihood like blue. Because if that player gets rent and „Go“ money, they can start to take back control. But with heavy hitters, you can still win every time with the worst Monopoly. The secret is in the money supply.

This video was an incredible undertaking, and I hope you enjoyed watching it as much as I enjoyed making it. It was many late nights, and I made both videos as short as I could while trying to leave no stone unturned. I hope that by watching this video and the one before it, you will become unstoppable in Monopoly. That is if you can get anyone to play with you.

From the bottom of my heart, thank you for your time watching this video, and I can’t wait to find out which game is asked for the most in the comments.